Gabriel Amadeus Tiller, 34, has been mapping trails since he was a kid. Now, his Portland, Oregon-based company, Limberlost, leads three bikepacking rides throughout the state, including the weeklong Oregon Outback (June 20-26, 2015; $2,100).

In which a cyclist breaks the law and the rules, becomes clairvoyant, partially inspires a life-changing metamorphosis, gets dropped bad—twice—and finally understands the meaning of mediocre amateur racing